I think it should be noted that getting a "bad" schedule is not the same thing as getting a "hard" schedule. A team may have the misfortune of playing against every powerhouse robot at the competition, which would be a hard schedule, but since the match scheduler was still outputting a variety of opponents it's not a bad schedule. I think a bad schedule indicates a situation in which the match scheduler broke - it didn't generate a schedule that fulfilled the necessary requirements. Playing with or against the same team repeatedly would indicate a bad schedule, regardless of how well that other team performed.
I have nothing more than anecdotes but it seems that the scheduler has been doing it's job the past few years. The only anomaly that I noticed was that 67 and 74 played against each other three or four times at West Michigan, but considering the size of the event and all of the other constraints I don't think that's considered a failure.
I'll admit that my team's match schedule at Waterford did make me groan a little bit, but that wasn't the scheduler's fault
